EP3099765B1 - The use of alkoxylated polyethylene glycols in lubricating oil compositions - Google Patents
The use of alkoxylated polyethylene glycols in lubricating oil compositions Download PDFInfo
- Publication number
- EP3099765B1 EP3099765B1 EP15702163.5A EP15702163A EP3099765B1 EP 3099765 B1 EP3099765 B1 EP 3099765B1 EP 15702163 A EP15702163 A EP 15702163A EP 3099765 B1 EP3099765 B1 EP 3099765B1
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- EP
- European Patent Office
- Prior art keywords
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- integer
- denotes
- polyethylene glycol
- ratio
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 73
- 229920001223 polyethylene glycol Polymers 0.000 title claims description 58
- 239000010687 lubricating oil Substances 0.000 title claims description 32
- 239000002202 Polyethylene glycol Substances 0.000 claims description 49
- 239000000314 lubricant Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- -1 defoamers Substances 0.000 description 90
- 239000002270 dispersing agent Substances 0.000 description 56
- 239000003921 oil Substances 0.000 description 48
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- 239000002585 base Substances 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 150000003904 phospholipids Chemical class 0.000 description 16
- 229920013639 polyalphaolefin Polymers 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 229960002317 succinimide Drugs 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000012530 fluid Substances 0.000 description 10
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 239000005864 Sulphur Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 230000001050 lubricating effect Effects 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- 239000004034 viscosity adjusting agent Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 239000004711 α-olefin Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 235000010338 boric acid Nutrition 0.000 description 6
- 229960002645 boric acid Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920002266 Pluriol® Polymers 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 150000001639 boron compounds Chemical class 0.000 description 5
- 239000010725 compressor oil Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000391 magnesium silicate Substances 0.000 description 5
- 229910052919 magnesium silicate Inorganic materials 0.000 description 5
- 235000019792 magnesium silicate Nutrition 0.000 description 5
- 238000005555 metalworking Methods 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 239000010705 motor oil Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000012264 purified product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 239000006078 metal deactivator Substances 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 239000000783 alginic acid Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 229950003621 butoxylate Drugs 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010689 synthetic lubricating oil Substances 0.000 description 3
- 239000010723 turbine oil Substances 0.000 description 3
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 2
- 229910011255 B2O3 Inorganic materials 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 229940069096 dodecene Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 150000002327 glycerophospholipids Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000010720 hydraulic oil Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 2
- 150000003905 phosphatidylinositols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
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- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- XCQXSYSIKVLBKE-UHFFFAOYSA-N nonyl heptanoate Chemical compound CCCCCCCCCOC(=O)CCCCCC XCQXSYSIKVLBKE-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- LQNPIBHEOATAEO-UHFFFAOYSA-N octanoate;octylazanium Chemical compound CCCCCCCCN.CCCCCCCC(O)=O LQNPIBHEOATAEO-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 238000005482 strain hardening Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000010729 system oil Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- IRKHIJIMXUBALO-UHFFFAOYSA-N triheptyl borate Chemical compound CCCCCCCOB(OCCCCCCC)OCCCCCCC IRKHIJIMXUBALO-UHFFFAOYSA-N 0.000 description 1
- KDQYHGMMZKMQAA-UHFFFAOYSA-N trihexyl borate Chemical compound CCCCCCOB(OCCCCCC)OCCCCCC KDQYHGMMZKMQAA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AZLXEMARTGQBEN-UHFFFAOYSA-N trinonyl borate Chemical compound CCCCCCCCCOB(OCCCCCCCCC)OCCCCCCCCC AZLXEMARTGQBEN-UHFFFAOYSA-N 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- ZAGXLQIHXTXRFW-UHFFFAOYSA-N tris(2-ethyl-4-methylhexyl)-tris(2-ethyl-4-methylhexyl)silyloxysilane Chemical compound CCC(C)CC(CC)C[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)O[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)CC(CC)CC(C)CC ZAGXLQIHXTXRFW-UHFFFAOYSA-N 0.000 description 1
- WAXLMVCEFHKADZ-UHFFFAOYSA-N tris-decyl borate Chemical compound CCCCCCCCCCOB(OCCCCCCCCCC)OCCCCCCCCCC WAXLMVCEFHKADZ-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
- C10M107/34—Polyoxyalkylenes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
- C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
- C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
- C10M2209/1065—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
- C10M2209/1075—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106 used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
Definitions
- the presently claimed invention is directed to the use of alkoxylated polyethylene glycols that are prepared by alkoxylating polyethylene glycol with at least one C 8 -C 30 epoxy alkane in lubricating oil compositions.
- Lubricating oil compositions are used in a variety of applications, such as industrial applications, transportation and engines.
- Industrial applications comprise of applications such as hydraulic oil, air compressor oil, gas compressor oil, gear oil, bearing and circulating system oil, refrigerator compressor oil and steam and gas turbine oils.
- Conventional lubricating oil compositions comprise base stocks, co-solvents and additives.
- the base stock is in each case selected according to the viscosity that is desired in the envisioned application. Combinations of base stocks of different viscosities, i.e. low and high viscosity respectively, are often used to adjust the needed final viscosity.
- the co-solvents are used to dissolve polar additives in usually less polar or unpolar base stocks.
- antioxidants are antioxidants, detergents, anti-wear additives, metal deactivator, corrosion inhibitors, friction modifiers, extreme-pressure additives, defoamers, anti-foaming agents, viscosity index improvers and demulsifying agents. These additives are used to impart further advantageous properties to the lubricating oil composition including longer stability and additional protection.
- lubricating oil compositions have to be replaced for various reasons such as lubricity loss and/or product degradation.
- machine engine, gearbox, compressor ⁇
- affinity of the lubricant components to adhere to the surface a certain residue of the lubricating oil composition (hold-up) remains in the machine, engine, gear etc. it is used in.
- the used and new lubricants are mixed with each other.
- compatibility between the old and new lubricant is very important.
- the efficiency can be increased if losses are minimized.
- the losses can be categorized in losses without and with load, their sum being the total losses.
- lubricant viscosity has a major effect on losses without load, i.e. spilling: Losses with load can be influenced by a low friction coefficient.
- energy efficiency strongly depends on the friction coefficient measured for a lubricant.
- the friction coefficient can be measured with several methods like Mini-Traction-Machine (MTM), SRV, 2 disc test rig etc.
- MTM Mini-Traction-Machine
- SRV Spin-V
- 2 disc test rig etc.
- the benefit of a MTM is that one can see the coefficient of friction as an influence of the slide roll ratio.
- Slide roll ratio describes the difference of the speeds of ball and disc used in the MTM.
- EP 141 473 A1 discloses the use of polyethers in lubricants.
- WO 1985/00182 A1 discloses polyethers that can be considered as a random polymer which is obtained by reacting a mixture comprising ethylene oxide, propylene oxide and a lower glycol to obtain an intermediate which is further reacted with an alpha-olefin.
- WO 1984/00361 A1 describes polyether that form a block copolymer comprising a block derived from ethylene oxide and propylene oxide and a block derived from C12-epoxide.
- YOGARAJ NABAR "Dow UCON(TM) Oil Soluble Polyalkylene Glycols, A New Type of Group V Base Oil Content", 8 TH INTERNATIONAL SYMPOSIUM ON FUELS AND LUBRICANTS, 1 March 2012 , discloses that the oil solubility of polyethers increases by increasing the carbon-to-oxygen ratio.
- alkoxylated polyethylene glycols which are derived from polyethylene glycol and at least one C 8 -C 30 epoxy alkane show a low friction coefficient and are compatible with base stocks that are conventionally used in lubricating oil compositions such as mineral oils and polyalphaolefins, preferably low viscosity polyalphaolefins, and consequently can be used for the formulation of lubricating oil compositions.
- the presently claimed invention is directed to the use of an alkoxylated polyethylene glycol of general formula (II) wherein
- lubricant in the sense of the presently claimed invention, is meant a substance capable of reducing friction between surfaces.
- branched denotes a chain of atoms with one or more side chains attached to it. Branching occurs by the replacement of a substituent, e.g., a hydrogen atom, with a covalently bonded alkyl radical.
- Alkyl radical denotes a moiety that is constituted solely of atoms of carbon and of hydrogen and does not contain any double bonds.
- inventively claimed alkoxylated polyethylene glycols are oil soluble, which means that, when mixed with mineral oils and/or polyalphaolefins, preferably low viscosity polyalphaolefins, in a weight ratio of 10:90, 50:50 and 90:10, the inventively claimed alkoxylated polyethylene glycols do not show phase separation after standing for 24 hours at room temperature for at least two weight rations out of the three weight ratios 10:90, 50:50 and 90:10.
- the alkoxylated polyethylene glycol as defined herein has a kinematic viscosity in the range of ⁇ 40 mm 2 /s to ⁇ 1300 mm 2 /s, more preferably in the range of ⁇ 50 mm 2 /s to ⁇ 1200 mm 2 /s, even more preferably in the range of ⁇ 70 mm 2 /s to ⁇ 1000 mm 2 /s, most preferably in the range of ⁇ 100 mm 2 /s to ⁇ 500 mm 2 /s, at 40 ° C, determined according to ASTM D 445.
- the alkoxylated polyethylene glycol as defined herein has a kinematic viscosity in the range of ⁇ 10 mm 2 /s to ⁇ 100 mm 2 /s, more preferably in the range of ⁇ 12 mm 2 /s to ⁇ 80 mm 2 /s, even more preferably in the range of ⁇ 14 mm 2 /s to ⁇ 65 mm 2 /s, most preferably in the range of ⁇ 15 mm 2 /s to ⁇ 60 mm 2 /s, at 100 ° C, determined according to ASTM D 445.
- the alkoxylated polyethylene glycol as defined herein has a viscosity index in the range of ⁇ 100 to ⁇ 300, more preferably in the range of ⁇ 120 to ⁇ 280, even more preferably in the range of ⁇ 140 to ⁇ 250, determined according to ASTM D 2270.
- the alkoxylated polyethylene glycol as defined herein has a viscosity index of 200 ⁇ 60, more preferably of 200 ⁇ 50, even more preferably of 200 ⁇ 40, most preferably of 200 ⁇ 30, determined according to ASTM D 2270.
- the alkoxylated polyethylene glycol as defined herein has a pour point in the range of ⁇ - 60 ° C to ⁇ 20 ° C, more preferably in the range of ⁇ - 50 ° C to ⁇ 15 ° C, even more preferably in the range of ⁇ - 50 ° C to ⁇ 5 ° C, most preferably in the range of ⁇ - -50 ° C to ⁇ - 5 ° C, determined according to DIN ISO 3016.
- the alkoxylated polyethylene glycol as defined herein has a weight average molecular weight Mw in the range of ⁇ 500 to ⁇ 20000 g/mol, more preferably in the range of ⁇ 2000 to ⁇ 15000 g/mol, even more preferably in the range of ⁇ 3000 to ⁇ 12000 g/mol determined, most preferably in the range of ⁇ 4000 to ⁇ 10000 g/mol, in particular in the range of ⁇ 4000 to ⁇ 8000 g/mol, determined according to DIN 55672-1.
- the alkoxylated polyethylene glycol as defined herein has a polydispersity in the range of ⁇ 1,05 to ⁇ 1,60, more preferably in the range of ⁇ 1,05 to ⁇ 1,50, most preferably in the range of ⁇ 1,10 to ⁇ 1,45, determined according to DIN 55672-1.
- the alkoxylated polyethylene glycol as defined herein has a hydroxyl number in the range of ⁇ 5 to ⁇ 50 mg KOH/g, more preferably in the range of ⁇ 5 to ⁇ 40 mg KOH/g, most preferably in the range of ⁇ 7 to ⁇ 35 mg KOH/g, determined according to DIN 53240.
- k is an integer in the range of ⁇ 3 to ⁇ 50, more preferably k is an integer in the range of ⁇ 3 to ⁇ 45, most preferably in the range of ⁇ 3 to ⁇ 40, even more preferably in the range of ⁇ 3 to ⁇ 30.
- m is an integer in the range of ⁇ 1 to ⁇ 25 and m' is an integer in the range of ⁇ 1 to ⁇ 25, more preferably m is an integer in the range of ⁇ 1 to ⁇ 20 and m' is an integer in the range of ⁇ 1 to ⁇ 20, even more preferably m is an integer in the range of ⁇ 3 to ⁇ 20 and m' is an integer in the range of ⁇ 3 to ⁇ 20, most preferably m is an integer in the range of ⁇ 4 to ⁇ 20 and m' is an integer in the range of ⁇ 4 to ⁇ 20.
- (m+m') is an integer in the range of ⁇ 3 to ⁇ 65, more preferably (m+m') is an integer in the range of ⁇ 3 to ⁇ 50, even more preferably (m+m') is an integer in the range of ⁇ 3 to ⁇ 40, most preferably (m+m') is an integer in the range of ⁇ 4 to ⁇ 40.
- the ratio of (m+m') to k is in the range of 0.5:1 to 4:1, most preferably in the range of 1:1 to 3:1, even more preferably in the range of 1:1 to 2:1, in particular in the range of 1.2:1 to 1.8:1.
- n is an integer in the range of ⁇ 3 to ⁇ 40 and n' is an integer in the range of ⁇ 3 to ⁇ 40, more preferably n is an integer in the range of ⁇ 3 to ⁇ 30 and n' is an integer in the range of ⁇ 3 to ⁇ 30, even more preferably n is an integer in the range of ⁇ 3 to ⁇ 20 and n' is an integer in the range of ⁇ 3 to ⁇ 20.
- (n+n') is an integer in the range of ⁇ 3 to ⁇ 60, more preferably (n+n') is an integer in the range of ⁇ 3 to ⁇ 40, even more preferably (n+n') is an integer in the range of ⁇ 5 to ⁇ 30.
- p is an integer in the range of ⁇ 3 to ⁇ 50 and p' is an integer in the range of ⁇ 3 to ⁇ 50, more preferably p is an integer in the range of ⁇ 3 to ⁇ 40 and p' is an integer in the range of ⁇ 3 to ⁇ 40, even more preferably p is an integer in the range of ⁇ 3 to ⁇ 30 and p' is an integer in the range of ⁇ 3 to ⁇ 30.
- (p+p') is an integer in the range of ⁇ 5 to ⁇ 90, more preferably (p+p') is an integer in the range of ⁇ 5 to ⁇ 80, even more preferably (p+p') is an integer in the range of ⁇ 5 to ⁇ 70.
- R 1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms. More preferably R 1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11, 12, 13, 14, 15 or 16 carbon atoms. Most preferably R 1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11 or 12 carbon atoms.
- the alkoxylated polyethylene glycol comprises units, wherein R 2 denotes -CH 2 -CH 3 , the ratio of (n+n') to k is in the range of 1:1 to 7:1, even more preferably in the range of 1:1 to 6:1, most preferably in the range of 2:1 to 6:1.
- the alkoxylated polyethylene glycol comprises units, wherein R 3 denotes -CH 3 , the ratio of (p+p') to k is in the range of 0.8:1 to 5:1, even more preferably in the range of 0.8:1 to 4:1, most preferably in the range of 1:1 to 3:1.
- the presently claimed invention is directed to the use of an alkoxylated polyethylene glycol of general formula (II) wherein
- the presently claimed invention is directed to the use of an alkoxylated polyethylene glycol of general formula (II) wherein
- the presently claimed invention is directed to the use of an alkoxylated polyethylene glycol of general formula (II) wherein
- the presently claimed invention is directed to the use of an alkoxylated polyethylene glycol of general formula (II) wherein
- the alkoxylated polyethylene glycols are obtained by reacting at least one polyethylene glycol block polymer with at least one C 8 -C 30 epoxy alkane and optionally at least one epoxide selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide in the presence of at least one catalyst.
- the at least one C 8 -C 30 epoxy alkane and the at least one epoxide selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide can either be added as a mixture of epoxides to obtain a random copolymer or in portions, whereby each portion contains a different epoxide, to obtain a block copolymer.
- the at least one C 8 -C 30 epoxy alkane is selected from the group consisting of 1,2-epoxyoctane; 1,2-epoxynonane; 1,2-epoxydecane; 1,2-epoxyundecane; 1,2-epoxydodecane; 1,2-epoxytridecane; 1,2-epoxytetradecane; 1,2-epoxypentadecane; 1,2-epoxyhexadecane; 1,2-epoxyheptadecane; 1,2-epoxyoctadecane; 1,2-epoxynonadecane; 1,2-epoxyicosane; 1,2-epoxyunicosane; 1,2-epoxydocosane; 1,2-epoxytricosane; 1,2-epoxytetracosane; 1,2-epoxypentacosane; 1,2-epoxyhexacosane; 1,2-epoxyheptacosane; 1,2-
- the at least one catalyst is a base or a double metal cyanide catalyst (DMC catalyst). More preferably the at least one catalyst is selected from the group consisting of alkaline earth metal hydroxides such as calcium hydroxide, strontium hydroxide and barium hydroxide, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide and caesium hydroxide and alkali metal alkoxylates such as potassium tert-butoxylate. Most preferably the at least one catalyst is sodium hydroxide or potassium tert-butoxylate. Most preferably the at least one catalyst is potassium tert-butoxylate.
- DMC catalyst double metal cyanide catalyst
- any inert solvents capable of dissolving alkoxylated polyethylene glycol and polyethylene glycol may be used as solvents during the reaction or as solvents required for working up the reaction mixture in cases where the reaction is carried out without solvents.
- the following solvents are mentioned as examples: methylene chloride, trichloroethylene, tetrahydrofuran, dioxane, methyl ethyl ketone, methylisobutyl ketone, ethyl acetate and isobutyl acetate.
- the amount of catalysts used is preferably in the range from 0.01 to 1.0, more preferably in the range from 0.05 to 0.5 % by weight, based on the total amount of the alkoxylated polyethylene glycol.
- the reaction is preferably carried out at a temperature in the range of 70 to 200° C, more preferably from 100 to 160° C.
- the pressure is preferably in the range from 1 bar to 150 bar, more preferably in the range from 3 to 30 bar.
- Such compounds are generally known and can be prepared, for example, by the process described in EP 0 862 947 B1 by combining the aqueous solution of a water-soluble metal salt with the aqueous solution of a hexacyanometallate compound, in particular of a salt or an acid, and, if necessary, adding a water-soluble ligand thereto either during or after the combination of the two solutions.
- DMC catalysts are usually prepared as a solid and used as such.
- the catalyst is typically used as powder or in suspension.
- the DMC catalyst is dispersed with an inert or non-inert suspension medium which can be, for example, the product to be produced or an intermediate by suitable measures, e.g. milling.
- the suspension produced in this way is used, if appropriate after removal of interfering amounts of water by methods known to those skilled in the art, e.g. stripping with or without use of inert gases such as nitrogen and/or noble gases.
- Suitable suspension media are, for example, toluene, xylene, tetrahydrofuran, acetone, 2-methylpentanone, cyclohexanone and also polyether alcohols according to the invention and mixtures thereof.
- the catalyst is preferably used in a suspension in a polyol as described, for example, in EP 0 090 444 A .
- the presently claimed invention is directed to the use of at least one alkoxylated polyethylene glycol as defined above or a mixture of polyethylene glycols as defined above for the preparation of a lubricating oil composition.
- the lubricating oil composition contains at least one alkoxylated polyethylene glycol in a small amount (when the alkoxylated polyethylene glycol is used as a friction modifier), in a medium amount (when the (when the alkoxylated polyethylene glycol is used as co-solvent) or in a large amount (when the alkoxylated polyethylene glycol is used as a base stock).
- the lubricating oil composition comprises ⁇ 1 % to ⁇ 10 % by weight or ⁇ 1 % to ⁇ 40 % by weight or ⁇ 20 % to ⁇ 100 % by weight, more preferably ⁇ 1 % to ⁇ 5 % by weight or ⁇ 1 % to ⁇ 35 % by weight or ⁇ 25 % to ⁇ 100 % by weight, most preferably ⁇ 1 % to ⁇ 2 % by weight or ⁇ 2 % to ⁇ 30 % by weight or ⁇ 30 % to ⁇ 100 % by weight, of at least one alkoxylated polyethylene glycol as defined above, related to the total amount of the lubricating oil composition.
- the lubricating oil composition according to the presently claimed invention has a friction coefficient in the range of ⁇ 0.003 to ⁇ 0.030, more preferably in the range of ⁇ 0.03 to ⁇ 0.028, even more preferably in the range of ⁇ 0.005 to ⁇ 0.027, most preferably in the range of ⁇ 0.010 to ⁇ 0.025 at 25% slide roll ratio (SRR), determined using mini-traction machine (MTM) measurements at 70 ° C and 1 GPa.
- SRR slide roll ratio
- the presently claimed invention relates to an industrial oil comprising at least one alkoxylated polyethylene glycol.
- Lubricating oil compositions comprising at least one alkoxylated polyethylene glycol as defined above or a mixture of polyethylene glycols as defined above can be used for various applications such as light, medium and heavy duty engine oils, industrial engine oils, marine engine oils, automotive engine oils, crankshaft oils, compressor oils, refrigerator oils, hydrocarbon compressor oils, very low-temperature lubricating oils and fats, high temperature lubricating oils and fats, wire rope lubricants, textile machine oils, refrigerator oils, aviation and aerospace lubricants, aviation turbine oils, transmission oils, gas turbine oils, spindle oils, spin oils, traction fluids, transmission oils, plastic transmission oils, passenger car transmission oils, truck transmission oils, industrial transmission oils, industrial gear oils, insulating oils, instrument oils, brake fluids, transmission liquids, shock absorber oils, heat distribution medium oils, transformer oils, fats, chain oils, minimum quantity lubricants for metalworking operations, oil to the warm and cold working, oil for water-based metalworking liquids, oil for neat oil metalworking fluids, oil for semi-s
- a lubricating oil composition can comprise of base stocks, co-solvents and a variety of different additives in varying ratios.
- the lubricating oil composition further comprises base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils).
- base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils).
- the lubricating oil comprises ⁇ 50 % to ⁇ 99 % by weight or ⁇ 80 % to ⁇ 99 % by weight or ⁇ 90 % to ⁇ 99 % by weight base stocks, related to the total amount of the lubricating oil composition.
- Group IV base stocks contain polyalphaolefins.
- Synthetic lower viscosity fluids suitable for the present invention include the polyalphaolefins (PAOs) and the synthetic oils from the hydrocracking or hydroisomerization of Fischer Tropsch high boiling fractions including waxes. These are both stocks comprised of saturates with low impurity levels consistent with their synthetic origin.
- the hydroisomerized Fischer Tropsch waxes are highly suitable base stocks, comprising saturated components of iso-paraffinic character (resulting from the isomerization of the predominantly n-paraffins of the Fischer Tropsch waxes) which give a good blend of high viscosity index and low pour point. Processes for the hydroisomerization of Fischer Tropsch waxes are described in U.S. Patents 5,362,378 ; 5,565,086 ; 5,246,566 and 5,135,638 , as well in EP 710710 , EP 321302 and EP 321304 .
- Polyalphaolefins suitable for the present invention include known PAO materials which typically comprise relatively low molecular weight hydrogenated polymers or oligomers of alphaolefins which include but are not limited to C 2 to about C 32 alphaolefins with the C 8 to about C 16 alphaolefins, such as 1-octene, 1-decene, 1-dodecene and the like being preferred.
- the preferred polyalphaolefins are poly-1-octene, poly-1-decene, and poly-1-dodecene, although the dimers of higher olefins in the range of C 14 to C 18 provide low viscosity base stocks.
- Low viscosity PAO fluids suitable for the present invention may be conveniently made by the polymerization of an alphaolefin in the presence of a polymerization catalyst such as the Friedel-Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
- a polymerization catalyst such as the Friedel-Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
- a polymerization catalyst such as the Friedel-Crafts catalysts including, for example,
- Patents 3,742,082 (Brennan ); 3,769,363 (Brennan ); 3,876,720 (Heilman ); 4,239,930 (Allphin ); 4,367,352 (Watts ); 4,413,156 (Watts ); 4,434,408 (Larkin ); 4,910,355 (Shubkin ); 4,956,122 (Watts ); and 5,068,487 (Theriot ).
- Group V base stocks contain any base stocks not described by Groups I to IV.
- Examples of Group V base stocks include alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters.
- Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly(1-decenes)); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulphides and derivative, analogs and homologs thereof.
- carboxylic acid esters suitable for the present invention include the esters of mono and polybasic acids with monoalkanols (simple esters) or with mixtures of mono and polyalkanols (complex esters), and the polyol esters of monocarboxylic acids (simple esters), or mixtures of mono and polycarboxylic acids (complex esters).
- Esters of the mono/polybasic type include, for example, the esters of monocarboxylic acids such as heptanoic acid, and dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc., with a variety of alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, or mixtures thereof with polyalkanols, etc.
- monocarboxylic acids such as heptanoic acid
- dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid,
- esters include nonyl heptanoate, dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, dibutyl -TMP- adipate, etc.
- esters such as those obtained by reacting one or more polyhydric alcohols, preferably the hindered polyols such as the neopentyl polyols, e.g. neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl-1,3-propanediol, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol with monocarboxylic acids containing at least 4 carbons, normally the C 5 to C 30 acids such as saturated straight chain fatty acids including caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures thereof, with polycarboxylic acids.
- the hindered polyols such as the neopentyl polyo
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These are exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and the alkyl and aryl ethers of polyoxyalkylene polymers (e.g., methyl-polyiso-propylene glycol ether having a molecular weight of 1000 or diphenyl ether of poly-ethylene glycol having a molecular weight of 1000 to 1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C 3 -C 8 fatty acid esters and C 13 Oxo acid diester of tetraethylene glycol.
- polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
- alkyl and aryl ethers of polyoxyalkylene polymers e.g.
- Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxysilicone oils and silicate oils comprise another useful class of synthetic lubricants; such oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethyl hexyl)silicate, tetra-(p-tert-butyl-phenyl) silicate, hexa-(4-methyl-2-ethylhexyl)disiloxane, oly(methyl)siloxanes and poly(methylphenyl)siloxanes.
- oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-eth
- Other synthetic lubricating oils include liquid esters of phosphorous-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
- the lubricating oil composition of the invention optionally further includes at least one other performance additive.
- the other performance additives include dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boronand/or sulphur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, friction modifiers and mixtures thereof.
- the total combined amount of the other performance additives (excluding the viscosity modifiers) present on an oil free basis may include ranges of 0 % by weight to 25 % by weight, or 0.01 % by weight to 20 % by weight, or 0.05 % by weight to 15 % by weight or 0.5 % by weight to 10 % by weight, or 1 to 5 % by weight of the composition.
- the other performance additives may be present, it is common for the other performance additives to be present in different amounts relative to each other.
- the lubricating composition further includes one or more viscosity modifiers.
- the viscosity modifier may be present in an amount of 0.5 % by weight to 70 % by weight, 1 % by weight to 60 % by weight, or 5 % by weight to 50 % by weight, or 10 % by weight to 50 % by weight of the lubricating composition.
- Viscosity modifiers include (a) polymethacrylates, (b) esterified copolymers of (II) a vinyl aromatic monomer and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) esterified interpolymers of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) hydrogenated copolymers of styrene-butadiene, (e) ethylene- propylene copolymers, (f) polyisobutenes, (g) hydrogenated styrene-isoprene polymers, (h) hydrogenated isoprene polymers, or (II) mixtures thereof.
- the viscosity modifier includes (a) a polymethacrylate, (b) an esterified copolymer of (II) a vinyl aromatic monomer; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) an esterified interpolymer of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) mixtures thereof.
- Extreme pressure agents include compounds containing boron and/or sulphur and/or phosphorus.
- the extreme pressure agent may be present in the lubricating composition at 0 % by weight to 20 % by weight, or 0.05 % by weight to 10 % by weight, or 0.1 % by weight to 8 % by weight of the lubricating composition.
- the extreme pressure agent is a sulphur- containing compound.
- the sulphur-containing compound may be a sulphurised olefin, a polysulphide, or mixtures thereof.
- the sulphurised olefin include a sulphurised olefin derived from propylene, isobutylene, pentene; an organic sulphide and/or polysulphide including benzyldisulphide; bis-(chlorobenzyl) disulphide; dibutyl tetrasulphide; di-tertiary butyl polysulphide; and sulphurised methyl ester of oleic acid, a sulphurised alkylphenol, a sulphurised dipentene, a sulphurised terpene, a sulphurised Diels-Alder adduct, an alkyl sulphenyl N',N- dialkyl dithi
- the sulphurised olefin includes a sulphurised olefin derived from propylene, isobutylene, pentene or mixtures thereof.
- the extreme pressure agent sulphur-containing compound includes a dimercaptothiadiazole or derivative, or mixtures thereof.
- dimercaptothiadiazole include compounds such as 2,5-dimercapto-1,3,4-thiadiazole or a hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazole, or oligomers thereof.
- the oligomers of hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazole typically form by forming a sulphur-sulphur bond between 2,5-dimercapto-1,3,4-thiadiazole units to form derivatives or oligomers of two or more of said thiadiazole units.
- Suitable 2,5-dimercapto-1,3,4-thiadiazole derived compounds include for example 2,5-bis(tert-nonyldithio)-1,3,4-thiadiazole or 2-tert-nonyldithio-5-mercapto-1,3,4-thiadiazole.
- the number of carbon atoms on the hydrocarbyl substituents of the hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazole typically include 1 to 30, or 2 to 20, or 3 to 16.
- the dimercaptothiadiazole may be a thiadiazole-functionalised dispersant.
- a detailed description of the thiadiazole- functionalised dispersant is described is paragraphs [0028] to [0052] of International Publication WO 2008/014315 .
- the thiadiazole-functionalised dispersant may be prepared by a method including heating, reacting or complexing a thiadiazole compound with a dispersant substrate.
- the thiadiazole compound may be covalently bonded, salted, complexed or otherwise solubilised with a dispersant, or mixtures thereof.
- the relative amounts of the dispersant substrate and the thiadiazole used to prepare the thiadiazole-functionalised dispersant may vary. In one embodiment the thiadiazole compound is present at 0.1 to 10 parts by weight relative to 100 parts by weight of the dispersant substrate. In different embodiments the thiadiazole compound is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or 0.2 to less than 5: to 100 parts by weight of the dispersant substrate.
- the relative amounts of the thiadiazole compound to the dispersant substrate may also be expressed as (0.1-10):100, or (>0.1-9):100, (such as (>0.5-9):100), or (0.1 to less than 5): 100, or (0.2 to less than 5): 100.
- the dispersant substrate is present at 0.1 to 10 parts by weight relative to 1 part by weight of the thiadiazole compound. In different embodiments the dispersant substrate is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or about 0.2 to less than 5: to 1 part by weight of the thiadiazole compound.
- the relative amounts of the dispersant substrate to the thiadiazole compound may also be expressed as (0.1-10):1, or (>0.1-9):1, (such as (>0.5-9):1), or (0.1 to less than 5): 1, or (0.2 to less than 5): 1.
- the thiadiazole-functionalised dispersant may be derived from a substrate that includes a succinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a polyisobutylene succinimide), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant, a polyetheramine dispersant, a viscosity modifier containing dispersant functionality (for example polymeric viscosity index modifiers (VMs) containing dispersant functionality), or mixtures thereof.
- the dispersant substrate includes a succinimide dispersant, an ester-containing dispersant or a Mannich dispersant.
- the extreme pressure agent includes a boron- containing compound.
- the boron-containing compound includes a borate ester (which in some embodiments may also be referred to as a borated epoxide), a borated alcohol, a borated dispersant, a borated phospholipid or mixtures thereof.
- the boron-containing compound may be a borate ester or a borated alcohol.
- the borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof.
- the alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms, i.e., vicinal.
- Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide and alkyl borates.
- the borate ester may also be prepared from boron halides.
- suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl borate.
- the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
- the boron-containing compound is a borated dispersant, typically derived from an N-substituted long chain alkenyl succinimide.
- the borated dispersant includes a polyisobutylene succinimide. Borated dispersants are described in more detail in US Patents 3,087,936 ; and Patent 3,254,025 .
- the borated dispersant may be used m combination with a sulphur-containing compound or a borate ester.
- the extreme pressure agent is other than a borated dispersant.
- the number average molecular weight of the hydrocarbon from which the long chain alkenyl group was derived includes ranges of 350 to 5000, or 500 to 3000, or 550 to 1500.
- the long chain alkenyl group may have a number average molecular weight of 550, or 750, or 950 to 1000.
- the N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide, and alkyl borates.
- boric acid for example, metaboric acid, orthoboric acid and tetraboric acid
- boric oxide for example, boron trioxide
- alkyl borates alkyl borates.
- the borating agent is boric acid which may be used alone or in combination with other borating agents.
- the borated dispersant may be prepared by blending the boron compound and the N-substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 80 ° C to 250 ° C, or 90 ° C to 230 ° C, or 100 ° C to 210 ° C, until the desired reaction has occurred.
- the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may have ranges including 10:1 to 1:4, or 4:1 to 1:3; or the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may be 1:2.
- the ratio of moles B : moles N (that is, atoms of B : atoms of N) in the borated dispersant may be 0.25:1 to 10:1 or 0.33:1 to 4:1 or 0.2:1 to 1.5:1, or 0.25:1 to 1.3:1 or 0.8:1 to 1.2:1 or about 0.5:1
- An inert liquid may be used in performing the reaction.
- the liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
- the lubricating composition further includes a borated phospholipid.
- the borated phospholipid may be derived from boronation of a phospholipid (for example boronation may be carried out with boric acid).
- Phospholipids and lecithins are described in detail in Encyclopedia of Chemical Technology, Kirk and Othmer, 3rd Editi on, in " Fats and Fatty Oils", Volume 9, pages 795-831 and in " Lecithins", Volume 14, pages 250-269 .
- the phospholipid may be any lipid containing a phosphoric acid, such as lecithin or cephalin, or derivatives thereof.
- phospholipids include phosphatidylcholine, phosphatidylserine, phosphatidylinositol, phosphatidylethanolamine, phosphotidic acid and mixtures thereof.
- the phospholipids may be glycerophospholipids, glycerol derivatives of the above list of phospholipids.
- the glycerophospholipids have one or two acyl, alkyl or alkenyl groups on a glycerol residue.
- the alkyl or alkenyl groups may contain 8 to 30, or 8 to 25, or 12 to 24 carbon atoms.
- alkyl or alkenyl groups examples include octyl, dodecyl, hexadecyl, octadecyl, docosanyl, octenyl, dodecenyl, hexadecenyl and octadecenyl.
- Phospholipids may be prepared synthetically or derived from natural sources. Synthetic phospholipids may be prepared by methods known to those in the art. Naturally derived phospholipids are often extracted by procedures known to those in the art. Phospholipids may be derived from animal or vegetable sources. A useful phospholipid is derived from sunflower seeds. The phospholipid typically contains 35 % to 60 % phosphatidylcholine, 20 % to 35 % phosphatidylinositol, 1 % to 25 % phosphatidic acid, and 10 % to 25 % phosphatidylethanolamine, wherein the percentages are by weight based on the total phospholipids.
- the fatty acid content may be 20 % by weight to 30 % by weight palmitic acid, 2 % by weight to 10 % by weight stearic acid, 15 % by weight to 25 % by weight oleic acid, and 40 % by weight to 55 % by weight linoleic acid.
- Friction modifiers may include fatty amines, esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, or fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines.
- esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, or fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines.
- the lubricating composition may contain phosphorus- or sulphur-containing antiwear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above.
- the antiwear agent may include a non-ionic phosphorus compound (typically compounds having phosphorus atoms with an oxidation state of +3 or +5), a metal dialkyldithiophosphate (typically zinc dialkyldithiophosphates), a metal mono- or di- alkylphosphate (typically zinc phosphates), or mixtures thereof.
- the non-ionic phosphorus compound includes a phosphite ester, a phosphate ester, or mixtures thereof.
- the lubricating composition of the invention further includes a dispersant.
- the dispersant may be a succinimide dispersant (for example N-substituted long chain alkenyl succinimides), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant or a polyetheramine dispersant.
- succinimide dispersant for example N-substituted long chain alkenyl succinimides
- Mannich dispersant for example N-substituted long chain alkenyl succinimides
- an ester-containing dispersant for example N-substituted long chain alkenyl succinimides
- the succinimide dispersant includes a polyisobutylene-substituted succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000, or 950 to 1600.
- Suitable ester-containing dispersants are typically high molecular weight esters. These materials are described in more detail in U.S. Patent 3,381,022 .
- the dispersant includes a borated dispersant.
- the borated dispersant includes a succinimide dispersant including a polyisobutylene succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000. Borated dispersants are described in more detail above within the extreme pressure agent description.
- Dispersant viscosity modifiers include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or esterified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- functionalised polyolefins for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or esterified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- Corrosion inhibitors include 1-amino-2-propanol, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and/or a fatty acid such as oleic acid with a polyamine.
- Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles.
- the metal deactivators may also be described as corrosion inhibitors.
- Foam inhibitors include copolymers of ethyl acrylate and 2-ethylhexyl acrylate and optionally vinyl acetate.
- Demulsifiers include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
- Pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides.
- Seal swell agents including Exxon Necton-37TM (FN 1380) and Exxon Mineral Seal OilTM (FN 3200).
- the lubricating oil composition contains co-solvents selected from the group consisting of di-isodecyl adipate, di-propyladipate, di-isotridecyl adipate, trimethylpropyl tricaprylate, di-isooctyl adipate, di-ethylhexyl adipate and d-inonyl adipate.
- the lubricating oil composition contains co-solvents in an amount of ⁇ 0.5 % to ⁇ 35 % by weight, more preferably ⁇ 1 % to ⁇ 30 % by weight, related to the overall weight of the lubricating oil composition.
- the kinematic viscosity was measured according to the standard international method ASTM D 445.
- the viscosity index was measured according to the ASTM D 2270.
- the pour point according was measured to DIN ISO 3016.
- the disc and ball used for the experiments were made of steel (AISI 52100), with a hardness of 750 HV and Ra ⁇ 0,02 ⁇ m.
- the diameter was 45,0 mm and 19,0 mm for the disc and the ball respectively.
- the tractions curves were run with 1,00 GPa contact pressure, 4 m/s mean speed and 70° C temperature.
- the slide-roll ratio (SRR) was varied from 0 to 25% and the friction coefficient measured.
- a method was developed in-house to determine oil compatibility.
- the oil and test material were mixed in 10/90, 50/50 and 90/10 % w/w ratios respectively.
- the mixtures were mixed at room temperature by rolling for 12 hours.
- the mixtures' appearance was observed after homogenization and again after 24 hours.
- the test material is deemed compatible with the oil when no phase separation is observed after 24 hours for at least two of the ratios investigated.
- Example 1 Pluriol® E400 with 12 equivalents of C12 epoxide and 20 equivalents of butylene oxide (random)
- a steel reactor (1,5 I) was loaded with polyethylene glycol 400 (MW 400) (0,2 mol, 80 g), and 3,23 g KOtBu (0,4 w%) was mixed and the reactor was purged with nitrogen.
- a pressure of 2 bar a mixture of butylene oxide and C12 epoxide (4,0 mol, 288 g BuO; 2,4 mol, 441 g C12 epoxide) was brought in dropwise during 10 h at 140 ° C and under pressure of 6 bar.
- the reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C.
- the product was stripped by nitrogen.
- Example 2 Pluriol® E200 with 12 equivalents of C12 epoxide and 20 equivalents butylene oxide (random)
- a steel reactor (1,5 I) was loaded with polyethylene glycol 200 (MW 200) (0,2 mol, 80 g), and 3,07 g KOtBu (0,4 w%) was mixed and the reactor was purged with nitrogen.
- a pressure of 2 bar a mixture of butylene oxide and C12 epoxide (4,0 mol, 288 g BuO; 2,4 mol, 441 g C12 epoxide) was brought in dropwise during 8 h at 140 ° C and under pressure of 6 bar.
- the reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C.
- the product was stripped by nitrogen.
- a steel reactor (1,5 I) was loaded with polyethylene glycol 1000 (MW 1000) (0,1 mol, 100 g), and 6,66 g CsOH 50 % in water (0,3 w% to product) was mixed and the reactor was purged with nitrogen.
- a pressure of 2 bar a mixture of propylene oxide and C12 epoxide (6,0 mol, 348 g PO; 3,6 mol, 662 g C12 epoxide) was brought in dropwise during 10 h at 140 ° C and under pressure of 6 bar.
- the reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C.
- the product was stripped by nitrogen.
- Example 4 Pluriol® E400 with 12 equivalents of C12 epoxide and 10 equivalents propylene oxide (random)
- a steel reactor (1,5 I) was loaded with polyethylene glycol 400 (MW 400) (0,25 mol, 100 g), and 1,6 g KOtBu (0,2 w%) was mixed and the reactor was purged with nitrogen.
- a pressure of 2 bar a mixture of propylene oxide and C12 epoxide (2,5 mol, 145 g PO; 3,0 mol, 552 g C12 epoxide) was brought in dropwise during 8 h at 140 ° C and under pressure of 6 bar.
- the reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C.
- the product was stripped by nitrogen.
- the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C.
- the purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 773 g (Theor.: 802 g) OHZ: 37,1 mg KOH/g; (Theo.: 35,2 mgKOH/g); GPC: Mn: 3586; Mw: 3738; Mp: 3816.
- a steel reactor (1,5 l) was loaded with polyethylene glycol 400 (MW 400) (0,35 mol, 140 g), and 1,6 g KOtBu (0,2 w%) was mixed and the reactor was purged with nitrogen.
- C12 epoxide (3,5 mol, 644 g) was brought in dropwise during 8 h at 140 ° C and under pressure of 6 bar.
- the reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C.
- the product was stripped by nitrogen.
- the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C.
- the purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 748 g (Theor.: 784 g) OHZ: 46,8 mg KOH/g; (Theo.: 50,1 mgKOH/g); GPC: Mn: 2650; Mw: 2742; Mp: 2735.
Description
- The presently claimed invention is directed to the use of alkoxylated polyethylene glycols that are prepared by alkoxylating polyethylene glycol with at least one C8-C30 epoxy alkane in lubricating oil compositions.
- Lubricating oil compositions are used in a variety of applications, such as industrial applications, transportation and engines. Industrial applications comprise of applications such as hydraulic oil, air compressor oil, gas compressor oil, gear oil, bearing and circulating system oil, refrigerator compressor oil and steam and gas turbine oils.
- Conventional lubricating oil compositions comprise base stocks, co-solvents and additives. The base stock is in each case selected according to the viscosity that is desired in the envisioned application. Combinations of base stocks of different viscosities, i.e. low and high viscosity respectively, are often used to adjust the needed final viscosity. The co-solvents are used to dissolve polar additives in usually less polar or unpolar base stocks.
- The most common additives are antioxidants, detergents, anti-wear additives, metal deactivator, corrosion inhibitors, friction modifiers, extreme-pressure additives, defoamers, anti-foaming agents, viscosity index improvers and demulsifying agents. These additives are used to impart further advantageous properties to the lubricating oil composition including longer stability and additional protection.
- However, after a certain operation time, lubricating oil compositions have to be replaced for various reasons such as lubricity loss and/or product degradation. Depending on the machine (engine, gearbox, compressor···) engineering design and the affinity of the lubricant components to adhere to the surface, a certain residue of the lubricating oil composition (hold-up) remains in the machine, engine, gear etc. it is used in. When being replaced by an unused and possibly different lubricating oil composition, the used and new lubricants are mixed with each other. Thus, in order to avoid any complications during operation, compatibility between the old and new lubricant is very important.
- Depending on their chemical properties a variety of components of lubricating oil compositions are incompatible with each other, i.e. the mixture of these components leads to oil gelling, phase separation, solidifying or foaming. The oil gelling leads to a dramatic increase of the viscosity which in turn can cause engine problems and can even require the engine to be replaced, if the damage is severe. Hence, when providing novel compounds that are used in lubricating oil compositions it should always be ensured that these compounds are compatible with compounds that are conventionally used in lubricating oil compositions.
- Besides compatibility with other lubricants, another area of concern is the energy efficiency. The efficiency can be increased if losses are minimized. The losses can be categorized in losses without and with load, their sum being the total losses. Within many parameters which can be influenced by geometry, material etc. lubricant viscosity has a major effect on losses without load, i.e. spilling: Losses with load can be influenced by a low friction coefficient. Thus, at a given viscosity, energy efficiency strongly depends on the friction coefficient measured for a lubricant.
- The friction coefficient can be measured with several methods like Mini-Traction-Machine (MTM), SRV, 2 disc test rig etc. The benefit of a MTM is that one can see the coefficient of friction as an influence of the slide roll ratio. Slide roll ratio describes the difference of the speeds of ball and disc used in the MTM.
-
EP 141 473 A1 -
WO 1985/00182 A1 -
WO 1984/00361 A1 - YOGARAJ NABAR: "Dow UCON(TM) Oil Soluble Polyalkylene Glycols, A New Type of Group V Base Oil Content", 8 TH INTERNATIONAL SYMPOSIUM ON FUELS AND LUBRICANTS, 1 March 2012, discloses that the oil solubility of polyethers increases by increasing the carbon-to-oxygen ratio.
- Thus, it was an objective of the presently claimed invention to provide compounds that show a low friction coefficient and that are compatible with base stocks, in particular base stocks such as mineral oils and polyalphaolefins, which are conventionally used in lubricating oil compositions for the preparation of lubricating oil compositions.
- Surprisingly, it has been found that alkoxylated polyethylene glycols which are derived from polyethylene glycol and at least one C8-C30 epoxy alkane show a low friction coefficient and are compatible with base stocks that are conventionally used in lubricating oil compositions such as mineral oils and polyalphaolefins, preferably low viscosity polyalphaolefins, and consequently can be used for the formulation of lubricating oil compositions.
-
- m is an integer in the range of ≥ 1 to ≤ 50,
- m' is an integer in the range of ≥ 1 to ≤ 50,
- (m+m') is an integer in the range of ≥ 3 to ≤ 65,
- n is an integer in the range of ≥ 0 to ≤ 75,
- n' is an integer in the range of ≥ 0 to ≤ 75,
- p is an integer in the range of ≥ 0 to ≤ 90,
- p' is an integer in the range of ≥ 0 to ≤ 90,
- k is an integer in the range of ≥ 2 to ≤ 50,
- R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
- By the term of "lubricant", in the sense of the presently claimed invention, is meant a substance capable of reducing friction between surfaces.
- As used herein, "branched" denotes a chain of atoms with one or more side chains attached to it. Branching occurs by the replacement of a substituent, e.g., a hydrogen atom, with a covalently bonded alkyl radical.
- "Alkyl radical" denotes a moiety that is constituted solely of atoms of carbon and of hydrogen and does not contain any double bonds.
- The inventively claimed alkoxylated polyethylene glycols are oil soluble, which means that, when mixed with mineral oils and/or polyalphaolefins, preferably low viscosity polyalphaolefins, in a weight ratio of 10:90, 50:50 and 90:10, the inventively claimed alkoxylated polyethylene glycols do not show phase separation after standing for 24 hours at room temperature for at least two weight rations out of the three weight ratios 10:90, 50:50 and 90:10.
- Preferably the alkoxylated polyethylene glycol as defined herein has a kinematic viscosity in the range of ≥ 40 mm2/s to ≤ 1300 mm2/s, more preferably in the range of ≥ 50 mm2/s to ≤ 1200 mm2/s, even more preferably in the range of ≥ 70 mm2/s to ≤ 1000 mm2/s, most preferably in the range of ≥ 100 mm2/s to ≤ 500 mm2/s, at 40 ° C, determined according to ASTM D 445.
- Preferably the alkoxylated polyethylene glycol as defined herein has a kinematic viscosity in the range of ≥ 10 mm2/s to ≤ 100 mm2/s, more preferably in the range of ≥ 12 mm2/s to ≤ 80 mm2/s, even more preferably in the range of ≥ 14 mm2/s to ≤ 65 mm2/s, most preferably in the range of ≥ 15 mm2/s to ≤ 60 mm2/s, at 100 ° C, determined according to ASTM D 445.
- Preferably the alkoxylated polyethylene glycol as defined herein has a viscosity index in the range of ≥ 100 to ≤ 300, more preferably in the range of ≥ 120 to ≤ 280, even more preferably in the range of ≥ 140 to ≤ 250, determined according to ASTM D 2270.
- Preferably the alkoxylated polyethylene glycol as defined herein has a viscosity index of 200 ± 60, more preferably of 200 ± 50, even more preferably of 200 ± 40, most preferably of 200 ± 30, determined according to ASTM D 2270.
- Preferably the alkoxylated polyethylene glycol as defined herein has a pour point in the range of ≥ - 60 ° C to ≤ 20 ° C, more preferably in the range of ≥ - 50 ° C to ≤ 15 ° C, even more preferably in the range of ≥ - 50 ° C to ≤ 5 ° C, most preferably in the range of ≥ - -50 ° C to ≤ - 5 ° C, determined according to DIN ISO 3016.
- The alkoxylated polyethylene glycol as defined herein has a weight average molecular weight Mw in the range of ≥ 500 to ≤ 20000 g/mol, more preferably in the range of ≥ 2000 to ≤ 15000 g/mol, even more preferably in the range of ≥ 3000 to ≤ 12000 g/mol determined, most preferably in the range of ≥ 4000 to ≤ 10000 g/mol, in particular in the range of ≥ 4000 to ≤ 8000 g/mol, determined according to DIN 55672-1.
- Preferably the alkoxylated polyethylene glycol as defined herein has a polydispersity in the range of ≥ 1,05 to ≤ 1,60, more preferably in the range of ≥ 1,05 to ≤ 1,50, most preferably in the range of ≥ 1,10 to ≤ 1,45, determined according to DIN 55672-1.
- Preferably the alkoxylated polyethylene glycol as defined herein has a hydroxyl number in the range of ≥ 5 to ≤ 50 mg KOH/g, more preferably in the range of ≥ 5 to ≤ 40 mg KOH/g, most preferably in the range of ≥ 7 to ≤ 35 mg KOH/g, determined according to DIN 53240.
- Preferably k is an integer in the range of ≥ 3 to ≤ 50, more preferably k is an integer in the range of ≥ 3 to ≤ 45, most preferably in the range of ≥ 3 to ≤ 40, even more preferably in the range of ≥ 3 to ≤ 30.
- Preferably m is an integer in the range of ≥ 1 to ≤ 25 and m' is an integer in the range of ≥ 1 to ≤ 25, more preferably m is an integer in the range of ≥ 1 to ≤ 20 and m' is an integer in the range of ≥ 1 to ≤ 20, even more preferably m is an integer in the range of ≥ 3 to ≤ 20 and m' is an integer in the range of ≥ 3 to ≤ 20, most preferably m is an integer in the range of ≥ 4 to ≤ 20 and m' is an integer in the range of ≥ 4 to ≤ 20.
- (m+m') is an integer in the range of ≥ 3 to ≤ 65, more preferably (m+m') is an integer in the range of ≥ 3 to ≤ 50, even more preferably (m+m') is an integer in the range of ≥ 3 to ≤ 40, most preferably (m+m') is an integer in the range of ≥ 4 to ≤ 40.
- The ratio of (m+m') to k is in the range of 0.5:1 to 4:1, most preferably in the range of 1:1 to 3:1, even more preferably in the range of 1:1 to 2:1, in particular in the range of 1.2:1 to 1.8:1.
- Preferably n is an integer in the range of ≥ 3 to ≤ 40 and n' is an integer in the range of ≥ 3 to ≤ 40, more preferably n is an integer in the range of ≥ 3 to ≤ 30 and n' is an integer in the range of ≥ 3 to ≤ 30, even more preferably n is an integer in the range of ≥ 3 to ≤ 20 and n' is an integer in the range of ≥ 3 to ≤ 20.
- Preferably (n+n') is an integer in the range of ≥ 3 to ≤ 60, more preferably (n+n') is an integer in the range of ≥ 3 to ≤ 40, even more preferably (n+n') is an integer in the range of ≥ 5 to ≤ 30.
- Preferably p is an integer in the range of ≥ 3 to ≤ 50 and p' is an integer in the range of ≥ 3 to ≤ 50, more preferably p is an integer in the range of ≥ 3 to ≤ 40 and p' is an integer in the range of ≥ 3 to ≤ 40, even more preferably p is an integer in the range of ≥ 3 to ≤ 30 and p' is an integer in the range of ≥ 3 to ≤ 30.
- Preferably (p+p') is an integer in the range of ≥ 5 to ≤ 90, more preferably (p+p') is an integer in the range of ≥ 5 to ≤ 80, even more preferably (p+p') is an integer in the range of ≥ 5 to ≤ 70.
- Preferably R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms. More preferably R1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11, 12, 13, 14, 15 or 16 carbon atoms. Most preferably R1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11 or 12 carbon atoms.
- In case the alkoxylated polyethylene glycol comprises units, wherein R2 denotes -CH2-CH3, the ratio of (n+n') to k is in the range of 1:1 to 7:1, even more preferably in the range of 1:1 to 6:1, most preferably in the range of 2:1 to 6:1.
- In case the alkoxylated polyethylene glycol comprises units, wherein R3 denotes -CH3, the ratio of (p+p') to k is in the range of 0.8:1 to 5:1, even more preferably in the range of 0.8:1 to 4:1, most preferably in the range of 1:1 to 3:1.
-
- m is an integer in the range of ≥ 1 to ≤ 30,
- m' is an integer in the range of ≥ 1 to ≤ 30,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is an integer in the range of ≥ 3 to ≤ 40,
- n' is an integer in the range of ≥ 3 to ≤ 40,
- (n+n') is an integer in the range of ≥ 6 to ≤ 40,
- p is an integer in the range of ≥ 0 to ≤ 75,
- p' is an integer in the range of ≥ 0 to ≤ 75,
- (p+p') is an integer in the range of ≥ 0 to ≤ 90,
- k is an integer in the range of ≥ 3 to ≤ 40,
- R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 30,
- m' is an integer in the range of ≥ 1 to ≤ 30,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is an integer in the range of ≥ 3 to ≤ 20,
- n' is an integer in the range of ≥ 3 to ≤ 20,
- (n+n') is an integer in the range of ≥ 6 to ≤ 30,
- p is an integer in the range of ≥ 0 to ≤ 75,
- p' is an integer in the range of ≥ 0 to ≤ 75,
- (p+p') is an integer in the range of ≥ 0 to ≤ 90,
- k is an integer in the range of ≥ 3 to ≤ 40,
- R1 denotes an unsubstituted, linear alkyl radical having 9, 10 or 11 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 30,
- m' is an integer in the range of ≥ 1 to ≤ 30,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is an integer in the range of ≥ 3 to ≤ 20,
- n' is an integer in the range of ≥ 3 to ≤ 20,
- (n+n') is an integer in the range of ≥ 6 to ≤ 30,
- p is an integer in the range of ≥ 0 to ≤ 75,
- p' is an integer in the range of ≥ 0 to ≤ 75,
- (p+p') is an integer in the range of ≥ 0 to ≤ 90,
- k is an integer in the range of ≥ 3 to ≤ 40,
- R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 30,
- m' is an integer in the range of ≥ 1 to ≤ 30,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is an integer in the range of ≥ 3 to ≤ 20,
- n' is an integer in the range of ≥ 3 to ≤ 20,
- (n+n') is an integer in the range of ≥ 6 to ≤ 30,
- p is an integer in the range of ≥ 0 to ≤ 75,
- p' is an integer in the range of ≥ 0 to ≤ 75,
- (p+p') is an integer in the range of ≥ 0 to ≤ 90,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 9, 10 or 11 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 25,
- m' is an integer in the range of ≥ 1 to ≤ 25,
- (m+m') is an integer in the range of ≥ 3 to ≤ 40,
- n is an integer in the range of ≥ 6 to ≤ 15,
- n' is an integer in the range of ≥ 6 to ≤ 15,
- (n+n') is an integer in the range of ≥ 12 to ≤ 25,
- p is an integer in the range of ≥ 0 to ≤ 25,
- p' is an integer in the range of ≥ 0 to ≤ 25,
- (p+p') is an integer in the range of ≥ 0 to ≤ 70,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11 or 12 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 25,
- m' is an integer in the range of ≥ 1 to ≤ 25,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is 0,
- n' is 0,
- p is an integer in the range of ≥ 3 to ≤ 45,
- p' is an integer in the range of ≥ 3 to ≤ 45,
- (p+p') is an integer in the range of ≥ 6 to ≤ 80,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 25,
- m' is an integer in the range of ≥ 1 to ≤ 25,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is 0,
- n' is 0,
- p is an integer in the range of ≥ 3 to ≤ 45,
- p' is an integer in the range of ≥ 3 to ≤ 45,
- (p+p') is an integer in the range of ≥ 6 to ≤ 80,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 9, 10 or 11 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 30,
- m' is an integer in the range of ≥ 1 to ≤ 30,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is 0,
- n' is 0,
- p is an integer in the range of ≥ 3 to ≤ 45,
- p' is an integer in the range of ≥ 3 to ≤ 45,
- (p+p') is an integer in the range of ≥ 6 to ≤ 80,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 25,
- m' is an integer in the range of ≥ 1 to ≤ 25,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is 0,
- n' is 0,
- p is an integer in the range of ≥ 3 to ≤ 40,
- p' is an integer in the range of ≥ 3 to ≤ 40,
- (p+p') is an integer in the range of ≥ 5 to ≤ 70,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11 or 12 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 1 to ≤ 25,
- m' is an integer in the range of ≥ 1 to ≤ 25,
- (m+m') is an integer in the range of ≥ 3 to ≤ 50,
- n is 0,
- n' is 0,
- p is an integer in the range of ≥ 3 to ≤ 40,
- p' is an integer in the range of ≥ 3 to ≤ 40,
- (p+p') is an integer in the range of ≥ 5 to ≤ 70,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 9, 10 or 11 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 2 to ≤ 25,
- m' is an integer in the range of ≥ 2 to ≤ 25,
- (m+m') is an integer in the range of ≥ 4 to ≤ 40,
- n is 0,
- n' is 0,
- p is an integer in the range of ≥ 4 to ≤ 40,
- p' is an integer in the range of ≥ 4 to ≤ 40,
- (p+p') is an integer in the range of ≥ 5 to ≤ 70,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 9, 10 or 11 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 2 to ≤ 25,
- m' is an integer in the range of ≥ 2 to ≤ 25,
- (m+m') is an integer in the range of ≥ 4 to ≤ 40,
- n is an integer in the range of ≥ 3 to ≤ 20,
- n' is an integer in the range of ≥ 3 to ≤ 20,
- (n+n') is an integer in the range of ≥ 6 to ≤ 30,
- p is 0,
- p' is 0,
- k is an integer in the range of ≥ 3 to ≤ 30,
- R1 denotes an unsubstituted, linear alkyl radical having 9, 10 or 11 carbon atoms,
- R2 denotes -CH2-CH3,
and - R3 denotes -CH3,
-
- m is an integer in the range of ≥ 2 to ≤ 25,
- m' is an integer in the range of ≥ 2 to ≤ 25,
- (m+m') is an integer in the range of ≥ 4 to ≤ 40,
- k is an integer in the range of ≥ 3 to ≤ 30,
and - R1 denotes an unsubstituted, linear or branched, alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms,
- The alkoxylated polyethylene glycols are obtained by reacting at least one polyethylene glycol block polymer with at least one C8-C30 epoxy alkane and optionally at least one epoxide selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide in the presence of at least one catalyst. In case at least one epoxide selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide is used, the at least one C8-C30 epoxy alkane and the at least one epoxide selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide can either be added as a mixture of epoxides to obtain a random copolymer or in portions, whereby each portion contains a different epoxide, to obtain a block copolymer.
- Preferably the at least one C8-C30 epoxy alkane is selected from the group consisting of 1,2-epoxyoctane; 1,2-epoxynonane; 1,2-epoxydecane; 1,2-epoxyundecane; 1,2-epoxydodecane; 1,2-epoxytridecane; 1,2-epoxytetradecane; 1,2-epoxypentadecane; 1,2-epoxyhexadecane; 1,2-epoxyheptadecane; 1,2-epoxyoctadecane; 1,2-epoxynonadecane; 1,2-epoxyicosane; 1,2-epoxyunicosane; 1,2-epoxydocosane; 1,2-epoxytricosane; 1,2-epoxytetracosane; 1,2-epoxypentacosane; 1,2-epoxyhexacosane; 1,2-epoxyheptacosane; 1,2-epoxyoctacosane; 1,2-epoxynonacosane and 1,2-epoxytriacontane.
- Preferably the at least one catalyst is a base or a double metal cyanide catalyst (DMC catalyst). More preferably the at least one catalyst is selected from the group consisting of alkaline earth metal hydroxides such as calcium hydroxide, strontium hydroxide and barium hydroxide, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide and caesium hydroxide and alkali metal alkoxylates such as potassium tert-butoxylate. Most preferably the at least one catalyst is sodium hydroxide or potassium tert-butoxylate. Most preferably the at least one catalyst is potassium tert-butoxylate.
- In case the catalyst is a base, any inert solvents capable of dissolving alkoxylated polyethylene glycol and polyethylene glycol may be used as solvents during the reaction or as solvents required for working up the reaction mixture in cases where the reaction is carried out without solvents. The following solvents are mentioned as examples: methylene chloride, trichloroethylene, tetrahydrofuran, dioxane, methyl ethyl ketone, methylisobutyl ketone, ethyl acetate and isobutyl acetate.
- In case the catalyst is a base, the amount of catalysts used is preferably in the range from 0.01 to 1.0, more preferably in the range from 0.05 to 0.5 % by weight, based on the total amount of the alkoxylated polyethylene glycol. The reaction is preferably carried out at a temperature in the range of 70 to 200° C, more preferably from 100 to 160° C. The pressure is preferably in the range from 1 bar to 150 bar, more preferably in the range from 3 to 30 bar.
- In case a DMC catalyst is used, it is in principle possible to use all types of DMC catalysts known from the prior art. Preference is given to using double metal cyanide catalysts of the general formula (1):
M1 a[M2(CN)b(A)c]d·fM1gXn.h(H2O).eL, (1)
wherein - M1 is a metal ion selected from the group comprising Zn2+, Fe2+, Co3+, Ni2+, Mn2+, Co2+, Sn2+, Pb2+, Mo4+, Mo6+, Al3+, V4+, V5+, Sr2+, W6+, Cr2+, Cr3+ and Cd2+,
- M2 is a metal ion selected from the group comprising Fe2+, Fe3+, Co2+, Co3+, Mn2+, Mn3+, V4+, V5+, Cr2+, Cr3+, Rh3+, Ru2+ and Ir3+,
- M1 and M2 are identical or different,
- A is an anion selected from the group comprising halide, hydroxide, sulfate, carbonate, cyanide, thiocyanate, isocyanate, cyanate, carboxylate, oxalate and nitrate,
- X is an anion selected from the group comprising halide, hydroxide, sulfate, carbonate, cyanide, thiocyanate, isocyanate, cyanate, carboxylate, oxalate and nitrate,
- L is a water-miscible ligand selected from the group comprising alcohols, aldehydes, ketones, ethers, poly- ethers, esters, ureas, amides, nitriles and sulfides,
and - a, b, c, d, g and n are selected so that the compound is electrically neutral
and - e is the coordination number of the ligand or zero,
- f is a fraction or integer greater than or equal to zero,
- h is a fraction or integer greater than or equal to zero.
- Such compounds are generally known and can be prepared, for example, by the process described in
EP 0 862 947 B1 by combining the aqueous solution of a water-soluble metal salt with the aqueous solution of a hexacyanometallate compound, in particular of a salt or an acid, and, if necessary, adding a water-soluble ligand thereto either during or after the combination of the two solutions. - DMC catalysts are usually prepared as a solid and used as such. The catalyst is typically used as powder or in suspension. However, other ways known to those skilled in the art for using catalysts can likewise be employed. In a preferred embodiment, the DMC catalyst is dispersed with an inert or non-inert suspension medium which can be, for example, the product to be produced or an intermediate by suitable measures, e.g. milling. The suspension produced in this way is used, if appropriate after removal of interfering amounts of water by methods known to those skilled in the art, e.g. stripping with or without use of inert gases such as nitrogen and/or noble gases. Suitable suspension media are, for example, toluene, xylene, tetrahydrofuran, acetone, 2-methylpentanone, cyclohexanone and also polyether alcohols according to the invention and mixtures thereof. The catalyst is preferably used in a suspension in a polyol as described, for example, in
EP 0 090 444 A . - In another embodiment, the presently claimed invention is directed to the use of at least one alkoxylated polyethylene glycol as defined above or a mixture of polyethylene glycols as defined above for the preparation of a lubricating oil composition.
- The lubricating oil composition contains at least one alkoxylated polyethylene glycol in a small amount (when the alkoxylated polyethylene glycol is used as a friction modifier), in a medium amount (when the (when the alkoxylated polyethylene glycol is used as co-solvent) or in a large amount (when the alkoxylated polyethylene glycol is used as a base stock).
- Preferably the lubricating oil composition comprises ≥ 1 % to ≤ 10 % by weight or ≥ 1 % to ≤ 40 % by weight or ≥ 20 % to ≤ 100 % by weight,
more preferably ≥ 1 % to ≤ 5 % by weight or ≥ 1 % to ≤ 35 % by weight or ≥ 25 % to ≤ 100 % by weight,
most preferably ≥ 1 % to ≤ 2 % by weight or ≥ 2 % to ≤ 30 % by weight or ≥ 30 % to ≤ 100 % by weight,
of at least one alkoxylated polyethylene glycol as defined above, related to the total amount of the lubricating oil composition. - Preferably, the lubricating oil composition according to the presently claimed invention has a friction coefficient in the range of
≥ 0.003 to ≤ 0.030, more preferably in the range of ≥ 0.03 to ≤ 0.028, even more preferably in the range of ≥ 0.005 to ≤ 0.027, most preferably in the range of ≥ 0.010 to ≤ 0.025 at 25% slide roll ratio (SRR), determined using mini-traction machine (MTM) measurements at 70 ° C and 1 GPa. - In another embodiment, the presently claimed invention relates to an industrial oil comprising at least one alkoxylated polyethylene glycol.
- Lubricating oil compositions comprising at least one alkoxylated polyethylene glycol as defined above or a mixture of polyethylene glycols as defined above can be used for various applications such as light, medium and heavy duty engine oils, industrial engine oils, marine engine oils, automotive engine oils, crankshaft oils, compressor oils, refrigerator oils, hydrocarbon compressor oils, very low-temperature lubricating oils and fats, high temperature lubricating oils and fats, wire rope lubricants, textile machine oils, refrigerator oils, aviation and aerospace lubricants, aviation turbine oils, transmission oils, gas turbine oils, spindle oils, spin oils, traction fluids, transmission oils, plastic transmission oils, passenger car transmission oils, truck transmission oils, industrial transmission oils, industrial gear oils, insulating oils, instrument oils, brake fluids, transmission liquids, shock absorber oils, heat distribution medium oils, transformer oils, fats, chain oils, minimum quantity lubricants for metalworking operations, oil to the warm and cold working, oil for water-based metalworking liquids, oil for neat oil metalworking fluids, oil for semi-synthetic metalworking fluids, oil for synthetic metalworking fluids, drilling detergents for the soil exploration, hydraulic oils, in biodegradable lubricants or lubricating greases or waxes, chain saw oils, release agents, moulding fluids, gun, pistol and rifle lubricants or watch lubricants and food grade approved lubricants.
- A lubricating oil composition can comprise of base stocks, co-solvents and a variety of different additives in varying ratios.
- Preferably the lubricating oil composition further comprises base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils). Preferably the lubricating oil comprises ≥ 50 % to ≤ 99 % by weight or ≥ 80 % to ≤ 99 % by weight or ≥ 90 % to ≤ 99 % by weight base stocks, related to the total amount of the lubricating oil composition.
- Definitions for the base stocks in this invention are the same as those found in the American Petroleum Institute (API) publication "Engine Oil Licensing and Certification System", Industry Services Department, Fourteenth Edition, December 1996, Addendum 1, December 1998. Said publication categorizes base stocks as follows:
- a) Group I base stocks contain less than 90 percent saturates and/or greater than 0.03 percent sulphur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in the following table
- b) Group II base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulphur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in the following table
- c) Group III base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulphur and have a viscosity index greater than or equal to 120 using the test methods specified in the following table
-
Property Test Method Saturates ASTM D 2007 Viscosity Index ASTM D 2270 Sulphur ASTM D 2622 ASTM D 4294 ASTM D 4927 ASTM D 3120 - Group IV base stocks contain polyalphaolefins. Synthetic lower viscosity fluids suitable for the present invention include the polyalphaolefins (PAOs) and the synthetic oils from the hydrocracking or hydroisomerization of Fischer Tropsch high boiling fractions including waxes. These are both stocks comprised of saturates with low impurity levels consistent with their synthetic origin. The hydroisomerized Fischer Tropsch waxes are highly suitable base stocks, comprising saturated components of iso-paraffinic character (resulting from the isomerization of the predominantly n-paraffins of the Fischer Tropsch waxes) which give a good blend of high viscosity index and low pour point. Processes for the hydroisomerization of Fischer Tropsch waxes are described in
U.S. Patents 5,362,378 ;5,565,086 ;5,246,566 and5,135,638 , as well inEP 710710 EP 321302 EP 321304 - Polyalphaolefins suitable for the present invention, as either lower viscosity or high viscosity fluids depending on their specific properties, include known PAO materials which typically comprise relatively low molecular weight hydrogenated polymers or oligomers of alphaolefins which include but are not limited to C2 to about C32 alphaolefins with the C8 to about C16 alphaolefins, such as 1-octene, 1-decene, 1-dodecene and the like being preferred. The preferred polyalphaolefins are poly-1-octene, poly-1-decene, and poly-1-dodecene, although the dimers of higher olefins in the range of C14 to C18 provide low viscosity base stocks.
- Low viscosity PAO fluids suitable for the present invention, may be conveniently made by the polymerization of an alphaolefin in the presence of a polymerization catalyst such as the Friedel-Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate. For example, the methods disclosed by
U.S. Patents 4,149,178 or3,382,291 may be conveniently used herein. Other descriptions of PAO synthesis are found in the followingU.S. Patents: 3,742,082 (Brennan );3,769,363 (Brennan );3,876,720 (Heilman );4,239,930 (Allphin );4,367,352 (Watts );4,413,156 (Watts );4,434,408 (Larkin );4,910,355 (Shubkin );4,956,122 (Watts ); and5,068,487 (Theriot ). - Group V base stocks contain any base stocks not described by Groups I to IV. Examples of Group V base stocks include alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters.
- Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly(1-decenes)); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulphides and derivative, analogs and homologs thereof.
- Further carboxylic acid esters suitable for the present invention include the esters of mono and polybasic acids with monoalkanols (simple esters) or with mixtures of mono and polyalkanols (complex esters), and the polyol esters of monocarboxylic acids (simple esters), or mixtures of mono and polycarboxylic acids (complex esters). Esters of the mono/polybasic type include, for example, the esters of monocarboxylic acids such as heptanoic acid, and dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc., with a variety of alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, or mixtures thereof with polyalkanols, etc. Specific examples of these types of esters include nonyl heptanoate, dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, dibutyl -TMP- adipate, etc.
- Also suitable for the present invention are esters, such as those obtained by reacting one or more polyhydric alcohols, preferably the hindered polyols such as the neopentyl polyols, e.g. neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl-1,3-propanediol, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol with monocarboxylic acids containing at least 4 carbons, normally the C5 to C30 acids such as saturated straight chain fatty acids including caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures thereof, with polycarboxylic acids.
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc., constitute another class of known synthetic lubricating oils. These are exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and the alkyl and aryl ethers of polyoxyalkylene polymers (e.g., methyl-polyiso-propylene glycol ether having a molecular weight of 1000 or diphenyl ether of poly-ethylene glycol having a molecular weight of 1000 to 1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters and C13 Oxo acid diester of tetraethylene glycol.
- Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxysilicone oils and silicate oils comprise another useful class of synthetic lubricants; such oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethyl hexyl)silicate, tetra-(p-tert-butyl-phenyl) silicate, hexa-(4-methyl-2-ethylhexyl)disiloxane, oly(methyl)siloxanes and poly(methylphenyl)siloxanes. Other synthetic lubricating oils include liquid esters of phosphorous-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
- The lubricating oil composition of the invention optionally further includes at least one other performance additive. The other performance additives include dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boronand/or sulphur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, friction modifiers and mixtures thereof.
- The total combined amount of the other performance additives (excluding the viscosity modifiers) present on an oil free basis may include ranges of 0 % by weight to 25 % by weight, or 0.01 % by weight to 20 % by weight, or 0.05 % by weight to 15 % by weight or 0.5 % by weight to 10 % by weight, or 1 to 5 % by weight of the composition.
- Although one or more of the other performance additives may be present, it is common for the other performance additives to be present in different amounts relative to each other.
- In one embodiment the lubricating composition further includes one or more viscosity modifiers.
- When present the viscosity modifier may be present in an amount of 0.5 % by weight to 70 % by weight, 1 % by weight to 60 % by weight, or 5 % by weight to 50 % by weight, or 10 % by weight to 50 % by weight of the lubricating composition.
- Viscosity modifiers include (a) polymethacrylates, (b) esterified copolymers of (II) a vinyl aromatic monomer and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) esterified interpolymers of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) hydrogenated copolymers of styrene-butadiene, (e) ethylene- propylene copolymers, (f) polyisobutenes, (g) hydrogenated styrene-isoprene polymers, (h) hydrogenated isoprene polymers, or (II) mixtures thereof.
- In one embodiment the viscosity modifier includes (a) a polymethacrylate, (b) an esterified copolymer of (II) a vinyl aromatic monomer; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) an esterified interpolymer of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) mixtures thereof.
- Extreme pressure agents include compounds containing boron and/or sulphur and/or phosphorus.
- The extreme pressure agent may be present in the lubricating composition at 0 % by weight to 20 % by weight, or 0.05 % by weight to 10 % by weight, or 0.1 % by weight to 8 % by weight of the lubricating composition.
- In one embodiment the extreme pressure agent is a sulphur- containing compound. In one embodiment the sulphur-containing compound may be a sulphurised olefin, a polysulphide, or mixtures thereof. Examples of the sulphurised olefin include a sulphurised olefin derived from propylene, isobutylene, pentene; an organic sulphide and/or polysulphide including benzyldisulphide; bis-(chlorobenzyl) disulphide; dibutyl tetrasulphide; di-tertiary butyl polysulphide; and sulphurised methyl ester of oleic acid, a sulphurised alkylphenol, a sulphurised dipentene, a sulphurised terpene, a sulphurised Diels-Alder adduct, an alkyl sulphenyl N',N- dialkyl dithiocarbamates; or mixtures thereof.
- In one embodiment the sulphurised olefin includes a sulphurised olefin derived from propylene, isobutylene, pentene or mixtures thereof.
- In one embodiment the extreme pressure agent sulphur-containing compound includes a dimercaptothiadiazole or derivative, or mixtures thereof. Examples of the dimercaptothiadiazole include compounds such as 2,5-dimercapto-1,3,4-thiadiazole or a hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazole, or oligomers thereof. The oligomers of hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazole typically form by forming a sulphur-sulphur bond between 2,5-dimercapto-1,3,4-thiadiazole units to form derivatives or oligomers of two or more of said thiadiazole units. Suitable 2,5-dimercapto-1,3,4-thiadiazole derived compounds include for example 2,5-bis(tert-nonyldithio)-1,3,4-thiadiazole or 2-tert-nonyldithio-5-mercapto-1,3,4-thiadiazole. The number of carbon atoms on the hydrocarbyl substituents of the hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazole typically include 1 to 30, or 2 to 20, or 3 to 16.
- In one embodiment the dimercaptothiadiazole may be a thiadiazole-functionalised dispersant. A detailed description of the thiadiazole- functionalised dispersant is described is paragraphs [0028] to [0052] of
International Publication WO 2008/014315 . - The thiadiazole-functionalised dispersant may be prepared by a method including heating, reacting or complexing a thiadiazole compound with a dispersant substrate. The thiadiazole compound may be covalently bonded, salted, complexed or otherwise solubilised with a dispersant, or mixtures thereof.
- The relative amounts of the dispersant substrate and the thiadiazole used to prepare the thiadiazole-functionalised dispersant may vary. In one embodiment the thiadiazole compound is present at 0.1 to 10 parts by weight relative to 100 parts by weight of the dispersant substrate. In different embodiments the thiadiazole compound is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or 0.2 to less than 5: to 100 parts by weight of the dispersant substrate. The relative amounts of the thiadiazole compound to the dispersant substrate may also be expressed as (0.1-10):100, or (>0.1-9):100, (such as (>0.5-9):100), or (0.1 to less than 5): 100, or (0.2 to less than 5): 100.
- In one embodiment the dispersant substrate is present at 0.1 to 10 parts by weight relative to 1 part by weight of the thiadiazole compound. In different embodiments the dispersant substrate is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or about 0.2 to less than 5: to 1 part by weight of the thiadiazole compound. The relative amounts of the dispersant substrate to the thiadiazole compound may also be expressed as (0.1-10):1, or (>0.1-9):1, (such as (>0.5-9):1), or (0.1 to less than 5): 1, or (0.2 to less than 5): 1.
- The thiadiazole-functionalised dispersant may be derived from a substrate that includes a succinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a polyisobutylene succinimide), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant, a polyetheramine dispersant, a viscosity modifier containing dispersant functionality (for example polymeric viscosity index modifiers (VMs) containing dispersant functionality), or mixtures thereof. In one embodiment the dispersant substrate includes a succinimide dispersant, an ester-containing dispersant or a Mannich dispersant.
- In one embodiment the extreme pressure agent includes a boron- containing compound. The boron-containing compound includes a borate ester (which in some embodiments may also be referred to as a borated epoxide), a borated alcohol, a borated dispersant, a borated phospholipid or mixtures thereof. In one embodiment the boron-containing compound may be a borate ester or a borated alcohol.
- The borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof. The alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms, i.e., vicinal.
- Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide and alkyl borates. The borate ester may also be prepared from boron halides.
- In one embodiment suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl borate. In one embodiment the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
- In one embodiment, the boron-containing compound is a borated dispersant, typically derived from an N-substituted long chain alkenyl succinimide. In one embodiment the borated dispersant includes a polyisobutylene succinimide. Borated dispersants are described in more detail in
US Patents 3,087,936 ; and Patent3,254,025 . - In one embodiment the borated dispersant may be used m combination with a sulphur-containing compound or a borate ester.
- In one embodiment the extreme pressure agent is other than a borated dispersant.
- The number average molecular weight of the hydrocarbon from which the long chain alkenyl group was derived includes ranges of 350 to 5000, or 500 to 3000, or 550 to 1500. The long chain alkenyl group may have a number average molecular weight of 550, or 750, or 950 to 1000.
- The N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide, and alkyl borates. In one embodiment the borating agent is boric acid which may be used alone or in combination with other borating agents.
- The borated dispersant may be prepared by blending the boron compound and the N-substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 80 ° C to 250 ° C, or 90 ° C to 230 ° C, or 100 ° C to 210 ° C, until the desired reaction has occurred. The molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may have ranges including 10:1 to 1:4, or 4:1 to 1:3; or the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may be 1:2. Alternatively, the ratio of moles B : moles N (that is, atoms of B : atoms of N) in the borated dispersant may be 0.25:1 to 10:1 or 0.33:1 to 4:1 or 0.2:1 to 1.5:1, or 0.25:1 to 1.3:1 or 0.8:1 to 1.2:1 or about 0.5:1 An inert liquid may be used in performing the reaction. The liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
- In one embodiment the lubricating composition further includes a borated phospholipid. The borated phospholipid may be derived from boronation of a phospholipid (for example boronation may be carried out with boric acid). Phospholipids and lecithins are described in detail in Encyclopedia of Chemical Technology, Kirk and Othmer, 3rd Edition, in "Fats and Fatty Oils", Volume 9, pages 795-831 and in "Lecithins", Volume 14, pages 250-269.
- The phospholipid may be any lipid containing a phosphoric acid, such as lecithin or cephalin, or derivatives thereof. Examples of phospholipids include phosphatidylcholine, phosphatidylserine, phosphatidylinositol, phosphatidylethanolamine, phosphotidic acid and mixtures thereof. The phospholipids may be glycerophospholipids, glycerol derivatives of the above list of phospholipids. Typically, the glycerophospholipids have one or two acyl, alkyl or alkenyl groups on a glycerol residue. The alkyl or alkenyl groups may contain 8 to 30, or 8 to 25, or 12 to 24 carbon atoms. Examples of suitable alkyl or alkenyl groups include octyl, dodecyl, hexadecyl, octadecyl, docosanyl, octenyl, dodecenyl, hexadecenyl and octadecenyl.
- Phospholipids may be prepared synthetically or derived from natural sources. Synthetic phospholipids may be prepared by methods known to those in the art. Naturally derived phospholipids are often extracted by procedures known to those in the art. Phospholipids may be derived from animal or vegetable sources. A useful phospholipid is derived from sunflower seeds. The phospholipid typically contains 35 % to 60 % phosphatidylcholine, 20 % to 35 % phosphatidylinositol, 1 % to 25 % phosphatidic acid, and 10 % to 25 % phosphatidylethanolamine, wherein the percentages are by weight based on the total phospholipids. The fatty acid content may be 20 % by weight to 30 % by weight palmitic acid, 2 % by weight to 10 % by weight stearic acid, 15 % by weight to 25 % by weight oleic acid, and 40 % by weight to 55 % by weight linoleic acid.
- Friction modifiers may include fatty amines, esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, or fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines.
- In one embodiment the lubricating composition may contain phosphorus- or sulphur-containing antiwear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above. Examples of the antiwear agent may include a non-ionic phosphorus compound (typically compounds having phosphorus atoms with an oxidation state of +3 or +5), a metal dialkyldithiophosphate (typically zinc dialkyldithiophosphates), a metal mono- or di- alkylphosphate (typically zinc phosphates), or mixtures thereof.
- The non-ionic phosphorus compound includes a phosphite ester, a phosphate ester, or mixtures thereof.
- In one embodiment the lubricating composition of the invention further includes a dispersant. The dispersant may be a succinimide dispersant (for example N-substituted long chain alkenyl succinimides), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant or a polyetheramine dispersant.
- In one embodiment the succinimide dispersant includes a polyisobutylene-substituted succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000, or 950 to 1600.
- Succinimide dispersants and their methods of preparation are more fully described in
U.S. Patents 4,234,435 and3,172,892 . - Suitable ester-containing dispersants are typically high molecular weight esters. These materials are described in more detail in
U.S. Patent 3,381,022 . - In one embodiment the dispersant includes a borated dispersant. Typically the borated dispersant includes a succinimide dispersant including a polyisobutylene succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000. Borated dispersants are described in more detail above within the extreme pressure agent description.
- Dispersant viscosity modifiers (often referred to as DVMs) include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or esterified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- Corrosion inhibitors include 1-amino-2-propanol, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and/or a fatty acid such as oleic acid with a polyamine.
- Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles. The metal deactivators may also be described as corrosion inhibitors.
- Foam inhibitors include copolymers of ethyl acrylate and 2-ethylhexyl acrylate and optionally vinyl acetate.
- Demulsifiers include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
- Pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides.
- Seal swell agents including Exxon Necton-37™ (FN 1380) and Exxon Mineral Seal Oil™ (FN 3200).
- Preferably the lubricating oil composition contains co-solvents selected from the group consisting of di-isodecyl adipate, di-propyladipate, di-isotridecyl adipate, trimethylpropyl tricaprylate, di-isooctyl adipate, di-ethylhexyl adipate and d-inonyl adipate. Preferably the lubricating oil composition contains co-solvents in an amount of ≥ 0.5 % to ≤ 35 % by weight, more preferably ≥ 1 % to ≤ 30 % by weight, related to the overall weight of the lubricating oil composition.
-
- OHZ = hydroxyl number, determined according to DIN 53240
- Mn= number average molecular weight, determined according to DIN 55672-1 and referred to Polystyrene calibration standard.
- Mw= weight average molecular weight, determined according to DIN 55672-1 and referred to Polystyrene calibration standard.
- PD = polydispersity, determined according to DIN 55672-1
- The kinematic viscosity was measured according to the standard international method ASTM D 445.
- The viscosity index was measured according to the ASTM D 2270.
- The pour point according was measured to DIN ISO 3016.
- The fluids were tested in the MTM (Mini-Traction Machine) instrument using the so-called traction test mode. In this mode, the friction coefficient is measured at a constant mean speed over a range of slide roll ratios (SRR) to give the traction curve. SRR = sliding speed /mean entrainment speed = 2 (U1-U2)/(U1+U2) in which U1 and U2 are the ball and disc speeds respectively
- The disc and ball used for the experiments were made of steel (AISI 52100), with a hardness of 750 HV and Ra < 0,02 µm. The diameter was 45,0 mm and 19,0 mm for the disc and the ball respectively. The tractions curves were run with 1,00 GPa contact pressure, 4 m/s mean speed and 70° C temperature. The slide-roll ratio (SRR) was varied from 0 to 25% and the friction coefficient measured.
- A method was developed in-house to determine oil compatibility. The oil and test material were mixed in 10/90, 50/50 and 90/10 % w/w ratios respectively. The mixtures were mixed at room temperature by rolling for 12 hours. The mixtures' appearance was observed after homogenization and again after 24 hours. The test material is deemed compatible with the oil when no phase separation is observed after 24 hours for at least two of the ratios investigated.
- A steel reactor (1,5 I) was loaded with polyethylene glycol 400 (MW 400) (0,2 mol, 80 g), and 3,23 g KOtBu (0,4 w%) was mixed and the reactor was purged with nitrogen. At a pressure of 2 bar a mixture of butylene oxide and C12 epoxide (4,0 mol, 288 g BuO; 2,4 mol, 441 g C12 epoxide) was brought in dropwise during 10 h at 140 ° C and under pressure of 6 bar. The reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C. The product was stripped by nitrogen. Then the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C. The purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 809 g, quantitative (Theor.: 809 g)
OHZ: 33,6 mg KOH/g; (Theo.: 27,7 mg KOH/g);
GPC: Mn: 3477; Mw: 3841; - A steel reactor (1,5 I) was loaded with polyethylene glycol 200 (MW 200) (0,2 mol, 80 g), and 3,07 g KOtBu (0,4 w%) was mixed and the reactor was purged with nitrogen. At a pressure of 2 bar a mixture of butylene oxide and C12 epoxide (4,0 mol, 288 g BuO; 2,4 mol, 441 g C12 epoxide) was brought in dropwise during 8 h at 140 ° C and under pressure of 6 bar. The reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C. The product was stripped by nitrogen. Then the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C. The purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 719 g, quantitative (Theor.: 769 g)
OHZ: 32,0 mg KOH/g; (Theo.: 29,2 mg KOH/g);
GPC: Mn: 3494; Mw: 3749; - A steel reactor (1,5 I) was loaded with polyethylene glycol 1000 (MW 1000) (0,1 mol, 100 g), and 6,66 g CsOH 50 % in water (0,3 w% to product) was mixed and the reactor was purged with nitrogen. At a pressure of 2 bar a mixture of propylene oxide and C12 epoxide (6,0 mol, 348 g PO; 3,6 mol, 662 g C12 epoxide) was brought in dropwise during 10 h at 140 ° C and under pressure of 6 bar. The reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C. The product was stripped by nitrogen. Then the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C. The purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 1125 g, quantitative (Theor.: 1110 g)
OHZ: 18,8 mg KOH/g; (Theo.: 10,1 mg KOH/g);
GPC: Mn: 5928; Mw: 7696; - A steel reactor (1,5 I) was loaded with polyethylene glycol 400 (MW 400) (0,25 mol, 100 g), and 1,6 g KOtBu (0,2 w%) was mixed and the reactor was purged with nitrogen. At a pressure of 2 bar a mixture of propylene oxide and C12 epoxide (2,5 mol, 145 g PO; 3,0 mol, 552 g C12 epoxide) was brought in dropwise during 8 h at 140 ° C and under pressure of 6 bar. The reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C. The product was stripped by nitrogen. Then the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C. The purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 773 g (Theor.: 802 g)
OHZ: 37,1 mg KOH/g; (Theo.: 35,2 mgKOH/g);
GPC: Mn: 3586; Mw: 3738; Mp: 3816. - A steel reactor (1,5 l) was loaded with polyethylene glycol 400 (MW 400) (0,35 mol, 140 g), and 1,6 g KOtBu (0,2 w%) was mixed and the reactor was purged with nitrogen. At a pressure of 2 bar C12 epoxide (3,5 mol, 644 g) was brought in dropwise during 8 h at 140 ° C and under pressure of 6 bar. The reactor was stirred for 10 h at 140 ° C and cooled to 80 ° C. The product was stripped by nitrogen. Then the product was discharged and mixed with Ambosol® (magnesium silicate, 30 g) and mixed on a rotary evaporator at 80 ° C. The purified product was obtained by filtration in a pressure strainer (Filtrations media: Seitz 900). Yield: 748 g (Theor.: 784 g)
OHZ: 46,8 mg KOH/g; (Theo.: 50,1 mgKOH/g);
GPC: Mn: 2650; Mw: 2742; Mp: 2735. - The oil compatibility and friction data are summarized in Table 1. The data demonstrate that the molecules derived from the present invention, namely polyalkylene glycols produced from the alkoxylation of polyethylene glycol (PEG) with epoxydodecane show compatibility with mineral oils and low viscosity polyalphaolefins whilst providing low friction coefficients (≤ 0,023 at 25% SRR in MTM experiments).
Table 1. Kinematic viscosity (mm2/s) Viscosity Index Pour point (°C) MTM friction coefficient at Mineral oil Group III compatibility at room temperature (oil/test material) Low viscosity PAO 6 compatibility at room temperature (oil/test material) 40°C 100°C 25% SSR 10/90 50/50 90/10 10/90 50/50 90/10 Example 1 190 26,7 176 -41 0,021 Yes Yes Yes Yes Yes No Example 2 203 27,1 170 -41 0,023 Yes Yes Yes Yes Yes Yes Example 3 366 53,2 212 -36 0,020 Yes Yes Yes Yes Yes Yes Example 4 140 22,0 186 -27 0,018 Yes Yes Yes Yes Yes Yes Example 5 112 17,9 178 -9 0,015 Yes Yes Yes Yes Yes Yes
wherein the alkoxylated polyethylene glycol has a weight average molecular weight Mw in the range of 500 to 20000 g/mol determined according to DIN 55672-1 (polystyrene calibration standard), and
wherein the ratio of (m+m') to k is in the range of 0.5:1 to 4:1,
wherein in case the alkoxylated polyethylene glycol comprises units, wherein R2 denotes - CH2-CH3 the ratio of (n+n') to k is in the range of 1:1 to 7:1,
wherein in case the alkoxylated polyethylene glycol comprises units, wherein R3 denotes - CH3 the ratio of (p+p') to k is in the range of 0.8:1 to 5:1,
as lubricant, which is capable of reducing friction between surfaces.
wherein the ratio of (m+m') to k is in the range of 1:1 to 2:1 and the ratio of (n+n') to k is in the range of 1:1 to 6:1, as a lubricant.
Claims (12)
- Use of an alkoxylated polyethylene glycol of general formula (II)m is an integer in the range of ≥ 1 to ≤ 50,m' is an integer in the range of ≥ 1 to ≤ 50,(m+m') is an integer in the range of ≥ 3 to ≤ 65,n is an integer in the range of ≥ 0 to ≤ 75,n' is an integer in the range of ≥ 0 to ≤ 75,p is an integer in the range of ≥ 0 to ≤ 90,p' is an integer in the range of ≥ 0 to ≤ 90,k is an integer in the range of ≥ 2 to ≤ 50,R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms,R2 denotes -CH2-CH3, andR3 denotes -CH3,whereby the concatenations denoted by k are distributed to form a block polymeric structure and the concatenations denoted by p, p', n, n', m and m' are distributed to form a block polymeric structure or a random polymeric structure,
wherein the alkoxylated polyethylene glycol has a weight average molecular weight Mw in the range of 500 to 20000 g/mol determined according to DIN 55672-1 (polystyrene calibration standard), and
wherein the ratio of (m+m') to k is in the range of 0.5:1 to 4:1,
wherein in case the alkoxylated polyethylene glycol comprises units, wherein R2 denotes -CH2-CH3 the ratio of (n+n') to k is in the range of 1:1 to 7:1,
wherein in case the alkoxylated polyethylene glycol comprises units, wherein R3 denotes -CH3 the ratio of (p+p') to k is in the range of 0.8:1 to 5:1,
as lubricant, which is capable of reducing friction between surfaces. - The use according to claim 1, wherein k is an integer in the range of ≥ 3 to ≤ 40.
- The use according to claim 1 or 2, wherein the alkoxylated polyethylene glycol has a weight average molecular weight Mw in the range of ≥ 2000 to ≤ 15000 g/mol determined according to DIN 55672-1 (polystyrene calibration standard).
- The use according to one more of claims 1 to 3, wherein (m+m') is in the range of ≥ 3 to ≤ 50.
- The use according to one more of claims 1 to 4, wherein the ratio of (m+m') to k is in the range of 1:1 to 3:1.
- The use according to one more of claims 1 to 5, wherein m is an integer in the range of ≥ 1 to ≤ 25 and m' is an integer in the range of ≥ 1 to ≤ 25.
- The use according to one more of claims 1 to 6, wherein R1 denotes an unsubstituted, linear alkyl radical having 8, 9, 10, 11, 12, 13, 14, 15, or 16 carbon atoms.
- The use according to claim 1, whereinm is an integer in the range of ≥ 1 to ≤ 30,m' is an integer in the range of ≥ 1 to ≤ 30,(m+m') is an integer in the range of ≥ 3 to ≤ 50,n is 0,n' is 0,p is an integer in the range of ≥ 0 to ≤ 90,p' is an integer in the range of ≥ 0 to ≤ 90,k is an integer in the range of ≥ 3 to ≤ 30,R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,R2 denotes -CH2-CH3,
andR3 denotes -CH3, - The use according to claim 8, wherein the ratio of (m+m') to k is in the range of 1:1 to 3:1 and the ratio of (p+p') to k is in the range of 0.8:1 to 4:1.
- The use according to claim 1, whereinm is an integer in the range of ≥ 1 to ≤ 30,m' is an integer in the range of ≥ 1 to ≤ 30,(m+m') is an integer in the range of ≥ 3 to ≤ 50,n is an integer in the range of ≥ 3 to ≤ 25,n' is an integer in the range of ≥ 3 to ≤ 25,(n+n') is an integer in the range of ≥ 6 to ≤ 35,p is 0,p' is 0,k is an integer in the range of ≥ 3 to ≤ 30,R1 denotes an unsubstituted, linear alkyl radical having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,R2 denotes -CH2-CH3,
andR3 denotes -CH3, - The use according to claim 10, wherein the ratio of (m+m') to k is in the range of 1:1 to 3:1 and the ratio of (n+n') to k is in the range of 1:1 to 6:1.
- The use according to claims 1 to 11 for reducing friction of a lubricating oil composition.
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Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SG11201509031RA (en) | 2013-05-02 | 2015-11-27 | Basf Se | Polyarylethersulfone copolymers |
US20160168504A1 (en) * | 2014-12-10 | 2016-06-16 | Hyundai Motor Company | Low viscosity gear oil composition providing enhanced fuel efficiency |
SG11201801166TA (en) * | 2015-08-13 | 2018-03-28 | Fuchs Petrolub Se | Composition for minimum quantity lubrication, and use of same |
JP6605948B2 (en) * | 2015-12-24 | 2019-11-13 | シェルルブリカンツジャパン株式会社 | Lubricating oil composition for internal combustion engines |
JP6823813B2 (en) * | 2017-07-11 | 2021-02-03 | 日油株式会社 | Lubricating oil composition |
FR3072969B1 (en) * | 2017-10-31 | 2019-11-22 | Total Marketing Services | LUBRICANT COMPOSITION LARGE COLD |
CN109593595A (en) * | 2018-12-20 | 2019-04-09 | 江苏二九建筑装饰工程有限公司 | A kind of environment-friendly water-soluble release agent |
US11697782B2 (en) * | 2020-07-09 | 2023-07-11 | ExxonMobil Technology and Engineering Company | Engine oil lubricant compositions and methods for making same with superior engine wear protection and corrosion protection |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1248643B (en) | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Process for the preparation of oil-soluble aylated amines |
NL135909C (en) | 1961-07-11 | |||
US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
US3382291A (en) | 1965-04-23 | 1968-05-07 | Mobil Oil Corp | Polymerization of olefins with bf3 |
US3742082A (en) | 1971-11-18 | 1973-06-26 | Mobil Oil Corp | Dimerization of olefins with boron trifluoride |
US3769363A (en) | 1972-03-13 | 1973-10-30 | Mobil Oil Corp | Oligomerization of olefins with boron trifluoride |
US3876720A (en) | 1972-07-24 | 1975-04-08 | Gulf Research Development Co | Internal olefin |
US4149178A (en) | 1976-10-05 | 1979-04-10 | American Technology Corporation | Pattern generating system and method |
US4234435A (en) | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
US4239930A (en) | 1979-05-17 | 1980-12-16 | Pearsall Chemical Company | Continuous oligomerization process |
JPS56126315A (en) | 1980-03-11 | 1981-10-03 | Sony Corp | Oscillator |
FR2491933B1 (en) * | 1980-10-10 | 1985-07-12 | Oreal | NOVEL POLYETHYLENE GLYCOLS DERIVATIVES, THEIR USE AND COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
US4367352A (en) | 1980-12-22 | 1983-01-04 | Texaco Inc. | Oligomerized olefins for lubricant stock |
JPS57140632A (en) * | 1981-02-25 | 1982-08-31 | Dai Ichi Kogyo Seiyaku Co Ltd | Dispersant for oily system |
US4956122A (en) | 1982-03-10 | 1990-09-11 | Uniroyal Chemical Company, Inc. | Lubricating composition |
AU551979B2 (en) | 1982-03-31 | 1986-05-15 | Shell Internationale Research Maatschappij B.V. | Epoxy polymerisation catalysts |
US4413156A (en) | 1982-04-26 | 1983-11-01 | Texaco Inc. | Manufacture of synthetic lubricant additives from low molecular weight olefins using boron trifluoride catalysts |
US4434308A (en) | 1982-04-28 | 1984-02-28 | Texaco Inc. | Manufacture of synthetic lubricant additives from internal olefins using boron trifluoride catalysis |
WO1984000361A1 (en) | 1982-07-08 | 1984-02-02 | Houghton & Co E F | Polyether thickeners for water-based hydraulic fluids |
GB2152529B (en) * | 1983-06-29 | 1986-11-19 | Houghton & Co E F | Water-based hydraulic fluid |
EP0141473A1 (en) | 1983-11-09 | 1985-05-15 | Akzo N.V. | Vulcanization method |
JPH06104640B2 (en) * | 1986-05-20 | 1994-12-21 | 第一工業製薬株式会社 | Process for producing polyoxyalkylene compound which is essentially compatible with non-aromatic hydrocarbon compound |
ES2054834T3 (en) | 1987-12-18 | 1994-08-16 | Exxon Research Engineering Co | METHOD FOR IMPROVING THE PERFORMANCE OF LUBRICATING OIL BY ISOMERIZATION OF PARAFFINS USING LOW COEFFICIENTS OF TREATMENT GAS. |
DE3870833D1 (en) | 1987-12-18 | 1992-06-11 | Exxon Research Engineering Co | METHOD FOR ISOMERIZING WAX TO LUBRICANT BASED USING AN ISOMERIZATION CATALYST. |
US4910355A (en) | 1988-11-02 | 1990-03-20 | Ethyl Corporation | Olefin oligomer functional fluid using internal olefins |
DK0458895T3 (en) | 1989-02-17 | 1995-11-06 | Chevron Usa Inc | Isomerization of waxy lubricating oils and petroleum wax using a silicoaluminophosphate molsi catalyst |
US5246566A (en) | 1989-02-17 | 1993-09-21 | Chevron Research And Technology Company | Wax isomerization using catalyst of specific pore geometry |
US5068487A (en) | 1990-07-19 | 1991-11-26 | Ethyl Corporation | Olefin oligomerization with BF3 alcohol alkoxylate co-catalysts |
US5362378A (en) | 1992-12-17 | 1994-11-08 | Mobil Oil Corporation | Conversion of Fischer-Tropsch heavy end products with platinum/boron-zeolite beta catalyst having a low alpha value |
US5736174A (en) * | 1994-03-14 | 1998-04-07 | Arco Chemical Technology, L.P. | Alkoxylated alcohol fat substitutes |
US5648557A (en) * | 1994-10-27 | 1997-07-15 | Mobil Oil Corporation | Polyether lubricants and method for their production |
US5565086A (en) | 1994-11-01 | 1996-10-15 | Exxon Research And Engineering Company | Catalyst combination for improved wax isomerization |
DE19709031A1 (en) | 1997-03-06 | 1998-09-10 | Basf Ag | Process for the preparation of double metal cyanide catalysts |
CN100516184C (en) * | 2003-03-24 | 2009-07-22 | 三洋化成工业株式会社 | Lubricant for water-miscible metal working oil |
CA2659250C (en) | 2006-07-27 | 2014-12-23 | The Lubrizol Corporation | Lubricating compositions comprising thiadiazole-functionalized dispersants |
WO2009045880A2 (en) * | 2007-09-28 | 2009-04-09 | Dow Global Technologies, Inc. | Functional fluid composition |
-
2015
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